D-glucopyranosyloxy)phenyl]-5,7-dihydroxy-
4'-beta-D-glucopyranosyloxy-5,7-dihydroxyisoflavone
CAS: 152-95-4
Molecular Formula: C21H20O10
D-glucopyranosyloxy)phenyl]-5,7-dihydroxy- - Names and Identifiers
| Name | 4'-beta-D-glucopyranosyloxy-5,7-dihydroxyisoflavone |
| Synonyms | ISOGENISTIN sophoricoside SOPHORICOSIDE GENISTEIN-4'-GLUCOSIDE GENISTEIN-4'-O-GLUCOSIDE 4H-1-Benzopyran-4-one,3-[4-(β- D-glucopyranosyloxy)phenyl]-5,7-dihydroxy- 4'-beta-D-glucopyranosyloxy-5,7-dihydroxyisoflavone 4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)phenyl beta-D-glucopyranoside 4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)phenyl alpha-L-gulopyranoside 5,7-dihydroxy-3-[4-[[3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]phenyl]-1-benzopyran-4-one |
| CAS | 152-95-4 |
| InChI | InChI=1/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-3-1-9(2-4-11)12-8-29-14-6-10(23)5-13(24)16(14)17(12)25/h1-6,8,15,18-24,26-28H,7H2/t15-,18+,19-,20-,21+/m0/s1 |
D-glucopyranosyloxy)phenyl]-5,7-dihydroxy- - Physico-chemical Properties
| Molecular Formula | C21H20O10 |
| Molar Mass | 432.38 |
| Density | 1.3597 (rough estimate) |
| Melting Point | 298° |
| Boling Point | 466.08°C (rough estimate) |
| Specific Rotation(α) | D20 -47° (pyridine); D20 -32° (10% aq pyridine) |
| Flash Point | 271.5°C |
| Solubility | Soluble in DMSO, pyridine, methanol |
| Vapor Presure | 1.7E-24mmHg at 25°C |
| Appearance | Yellow powder |
| Color | White to Light Brown |
| Maximum wavelength(λmax) | ['271nm(MeOH)(lit.)'] |
| pKa | 6.45±0.20(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
| Refractive Index | 1.5376 (estimate) |
| MDL | MFCD01075138 |
| Physical and Chemical Properties | White crystalline powder, soluble in methanol, derived from sophorae fructus. |
| In vitro study | Sophoricoside is an isoflavone glycoside isolated from Sophora japonica and has anti-inflammatory, anti-cancer and immunosuppressive effects. The results show that Sophoricoside (50 μM) significantly inhibits the PMACI-induced histamine release. The inhibition rate reaches up to 30.24%. The maximal rates of TNF-α, IL-8 and IL-6 inhibition by Sophoricoside (50 μM) are approximately 31.42%, 43.43% and 34.24%, respectively. The rates of the levels of Rel/p65 inhibition in nuclear by Sophoricoside (50 μM) is approximately 50.14%. Results show that the enhanced caspase-1 activity induced by PMACI is significantly reduced by Sophoricoside in a dose-dependent manner. |
| In vivo study | When the Sophoricoside is orally administered 1 h before compound 48/80 injections, the scratching behaviors is reduced. The inhibition rate of Sophoricoside (2 mg/kg) is approximately 41.21%. Orally administered Sophoricoside inhibits the scratching behaviors by 47.31%. When mice are treated for 2 weeks with Sophoricoside, the atopic dermatitis is recovered to a significant extent. |
D-glucopyranosyloxy)phenyl]-5,7-dihydroxy- - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| HS Code | 29329990 |
D-glucopyranosyloxy)phenyl]-5,7-dihydroxy- - Reference
| Reference Show more | 1. Niu Xiaojing, Lu Jing, Ma Yanjiang, et al. Optimization of Processing Technology of Sophora japonica Based on Multi-index General Evaluation and Naturalization [J]. Chinese Journal of Traditional Chinese Medicine, 2019, v.37(11):59-62. 2. Wang Kaichao, Mo Yingning, He Lingjian. Study on Preparation of High Purity Sophora japonica by Ultrasonic Extraction-Reversed Phase Medium Pressure Liquid Phase. 3. Wang Kaichao, Mo Yingning, He Lingjian. Preparation of high purity sophoricoside by ultrasonic extraction-reversed phase medium pressure liquid phase [J]. Shandong Journal of Traditional Chinese Medicine, 2020,39(08):868-873. |
D-glucopyranosyloxy)phenyl]-5,7-dihydroxy- - Reference Information
| Plant source: | Sophora japonica |
| overview | modern pharmacological research shows that sophoricoside has a good effect on lowering alanine aminotransferase in patients with chronic hepatitis, and can also inhibit ear edema induced by croton oil and claw edema caused by carrageenan. Clinical studies have also confirmed that sophoricoside can be used to prevent and treat the symptoms of postmenopausal osteoporosis in women. |
| biological activity | Sophoricoside is an isoflavone glycoside isolated from Sophora japonica, which has anti-inflammatory, anti-cancer and immunosuppressive effects. |
| use | blood sugar raising effect; Sophora japonica is soaked and injected into rabbits, which can temporarily increase blood sugar. According to the Nanjing Institute of Materia Medica, the genistein and kaempferol proposed from Sophora horns have the effects of interfering with the transportation of pregnant eggs, terminating the implantation of pregnant eggs, and anti-early pregnancy, which may be related to their estrogen activity; a small amount of long-term use Genistein and sophorin have a significant anti-fertility effect on female mice without affecting the mating rate and growth. Toxic effect, Sophora japonica dipping lamb can reduce the red blood cells of rabbits and guinea pigs, especially the pod effect. Sophora japonica seed extract can agglutinate red blood cells of rabbits, pigs and humans. The seeds, pods and pulp all contain anti-A, anti-B and anti-H agglutinin. Sophora japonica is a drug containing phytohemagglutinin and has the effect of promoting lymphocyte transformation |
Last Update：2024-04-09 21:54:55
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View History
D-glucopyranosyloxy)phenyl]-5,7-dihydroxy-
2,3-dihydro-2-thioxo-1H-Benzimidazole-5-carboxylic acid ethyl ester
8-Chloroimidazo[1,2-a]pyridine
51659-38-2
o-((piperidin-1-yl)methyl)benzyl alcohol(HCl)
3-CHLORO-2-METHYL-N-(2-HYDROXY-3-METHOXYBENZYLIDENE)ANILINE
4-{[6-(2-fluoroanilino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]amino}-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
1-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl](methyl)amino}-3-(phenylsulfanyl)pyrrolidine-2,5-dione
153915-56-1
3-Bromo-2-bromomethyl-6-(trifluoromethyl)pyridine
2,3-dihydro-2-thioxo-1H-Benzimidazole-5-carboxylic acid ethyl ester
8-Chloroimidazo[1,2-a]pyridine
51659-38-2
o-((piperidin-1-yl)methyl)benzyl alcohol(HCl)
3-CHLORO-2-METHYL-N-(2-HYDROXY-3-METHOXYBENZYLIDENE)ANILINE
4-{[6-(2-fluoroanilino)[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]amino}-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
1-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl](methyl)amino}-3-(phenylsulfanyl)pyrrolidine-2,5-dione
153915-56-1
3-Bromo-2-bromomethyl-6-(trifluoromethyl)pyridine